Just one look and no one is surprised that People magazine named Patrick Dempsey “Sexiest Men Alive” two years in a row. The “Grey’s Anatomy” heartthrob met his wife Jillian Fink, a celebrity stylist. He sat in her chair, and they married in 1999. They have three children and a loving family. But in 2015, Jillian filed for divorce after a scandal blew up.
Dempsey reconciled with his wife, choosing his family-man lifestyle over an extramarital affair with a “Grey’s Anatomy” staffer.
Katy Perry & Orlando Bloom
Katy Perry and Orlando Bloom met at the 2016 Golden Globes over an In-N-Out hamburger. Bloom nabbed it from Perry’s table. She talked to him about it, and he fell in love with her quirky sense of humor. She wanted to know if those grilled onions were still in his molars.
A year later, the lovebirds hit a roadblock when a scandalous photo of Bloom with Selena Gomez surfaced. Perry and Bloom put it behind them within a few months. They welcomed baby Daisy in 2020.
Kylie Jenner and Travis Scott's Bumpy Ride
Kylie and rapper Travis Scott met at the Coachella music festival in 2017. He introduced himself with a kiss, according to a festival attendee. A few months later they inked matching tats. And a year later, they welcomed a baby girl.
The billionaire beauty product maven and “Keeping Up With the Kardashians” star has had to face Scott being unfaithful to her which almost ended in divorce. It hasn’t been a smooth ride, but another baby on the way brought him home again.
Pink V Carey Hart
On their 12th wedding anniversary, Pink told Instagram that she and Carey Hart would have had 16 years together “if you count the 4 years we spent deciding if we were going to live together forever or kill each other.” The pair met in 2001 at the X Games. They broke up briefly in 2003 but then married in 2006.
The singer and the motocross racer split, yet again, in 2008, divorce papers and all, she even wrote some songs about it. After 11 months apart, they’ve been back together ever since.
The Three-Time Breakup of Gigi Hadid and Zayn Malik
Supermodel Gigi Hadid and popstar Zayn Malik have been a pair to watch. Not only are they one of the most beautiful showbiz couples, featured on the cover of every leading fashion magazine, but their relationship has dished some serious drama too. This includes three breakups: 2016, 2018, and 2019.
They met in 2015 and welcomed a baby girl in 2020. When Gigi met the former One Direction bandmember, she walked away from Joe Jonas and dove into a whirlwind romance with Zayn. Marriage rumors yet churn.
Hilary Duff and Matthew Koma
Matthew Koma is a musician and a record producer. He met Hilary Duff in the recording studio working on her album “Breath In. Breath Out.” At first, it was a working relationship, but soon they began dating.
By 2018, they welcomed a baby girl and by 2019, everyone was ogling over the former Disney diva’s wedding gown. The split happened in 2017 while Koma was on tour, but it didn’t last long.
The Almighty Ben Affleck and Jennifer Lopez
A secret romance took root playing partners-in-crime in the 2003 gangster movie flop. Rumors took off. Meanwhile, Affleck denied, denied, denied it, saying they’re just “really, really, really good friends.” Jennifer was married to Chris Judd, so PDAs were on the no-fly list. Shortly after however, from 2002 to 2004, they were the hottest couple in showbiz. Thus the birth of "Bennifer."
Bennifer broke up big-time in 2004. The split lasted 17 years! A hard pill to swallow, even though we loved Ben and his new Jen (Garner, duh.) Still, as it was written in the stars, J-Lo and Ben would reunite once more. Flashforward and not only are they back together again! They got married in an intimate ceremony in Las Vegas in July of 2022.
Beyoncé and Jay-Z
Beyoncé sat down with Orpah and talked about how friendship is the foundation of their relationship. The pop stars were friends first for over a year. Beyoncé told the media queen, “I would not be the woman I am if I did not go home to that man.” But it was not always smooth sailing. A 2005 scandal rocked Beyoncé's world. It inspired her to write “Resentment,” a song about how it feels. Reliable rumors said he was with Rhianna.
Jay-Z responded eventually with his own album. The rapper admitted to being unfaithful and apologized. In the end, surviving it all has made their marriage strong.
Courtney Cox and Johnny McDaid's Long-Distance Relationship
This couple began dating in 2013. They were engaged and then unengaged. Things were going well for the twosome until they wound up stuck living apart; with Johnny McDaid in Europe and Courtney in N.Y.C.
The 2020 lockdowns were to blame, but the “Friends” actress and musician joyously reunited at the end of 2020.
Phil Collins and Orianne Cevey's divorce settlement
It wasn’t the first time Phil Collins and Orianne Cevey broke up, but it was the biggest-ever UK celebrity divorce at $46 million. The classic rock superstar met Orianne in 1994. Fluent in four languages, she worked on his tour as a translator. The 1999 marriage hit rock bottom seven years into it.
The monster divorce payout didn’t stop him from reuniting with her within 10 years. It took a turn to the worst after the singer sank into squalor. Zero hygiene plus his aggressive behavior ended it for good.
The Onset of Cardi B and Offset
Cardi B and Offset secretly eloped in Atlanta in 2017. They married under Belcalis Marlenis Almanzar and Kiari Kendrell Cephus, which are their actual names. The rappers, each worth about $25M, soon welcomed baby girl Kulture. But then, a year into matrimony, Cardi B ditched her 8-carat diamond ring for a breakup.
Offset apologized publicly, saying he had one wish for his birthday—for Cardi to take him back. By February 2019, the 8-carat rock returned to its proper location, her finger.
Hailey Baldwin and Justin Bieber
The momentous event occurred in private at a courthouse in New York City. A year later, the two celebrated with friends and family. After years of Selena Gomez's drama, Bieber settled down with Hailey Baldwin.
He broke it off, temporarily, for one last try with Selena. Hailey and Justin prevailed. The happily-ever-after celeb duo married in 2018.
Gabrielle Union and Dwayne Wade
She’s an A-list celebrity and he’s an NBA superstar, put them together and you’ve got a media darling power couple. They met quietly at a Super Bowl party in 2007. Two years later they came out as a couple.
Flash forward to 2013, and the couple split. By the end of the year, Dwayne Wade proposed to Gabrielle Union with an 8.5-carat diamond ring. They sealed the deal in Miami on August 14, 2014. It includes a prenup on Union’s end.
The Osbourne’s Marriage
Staying married to rocker Ozzy Osbourne has been quite challenging, according to his wife. And he’s proven it on the family’s MTV reality show. Ozzy has been unfaithful and an excessively rancorous partner since they married in 1982.
A lot can happen in 30-plus years of marriage and Sharon Osbourne has shared the stories. After his latest scandal in 2017, they patched it up with a new diamond-studded wedding band and Ozzy promising not to cheat again.
Prince William and Kate Middleton
The engagement news lit up the media. Prince William and Kate Middleton’s 2011 wedding was even more spectacular. That is until the royal couple announced the birth of Prince George, and then Princess Charlotte two years later. Baby brother Prince Louis arrived in 2018.
It was also a major news event when William and Kate, who met at the University of St. Andrews, ended it two years after graduating college. It was a brief departure from the romance that kindled in 2004.
The Power Couple John Legend and Chrissy Teigen
But they’ve had some ups and downs. It was on the set of John Legend’s music video “Stereo” where they met. Chrissy Teigen was his love interest and he’s still interested. They started out texting, long-distance, and talking on the phone while Legend toured.
He freaked out for a day, panicking about getting tied down in a relationship, and called it all off. He got his senses back and by Christmas 2011, he surprised a with the ring in the Maldives.
Jean-Claude Van Damme and Gladys Portugues
Jean-Claude Van Damme and Gladys Portugues love each other so much they married twice. But they almost divorced twice too. The pair remarried in 1999 and things went well for about 15 years.
Then, it almost fell apart. Gladys filed the divorce papers in 2015, but they pulled it together. Van Damme said love won.
Adam Levine and Supermodel Behati Prinsloo
Behati said, “it was love at first sight.” Maroon 5 singer Adam Levine and Behati Prinsloo came out as a couple at a “GQ” event in 2012. It was smooth sailing until springtime. They broke up for a couple of months until they realized that parting was their worst decision. A whirlwind found them making up, engaging, and marrying within a year.
Nestled into the Santa Monica Mountains in the Pacific Palisades, they live happily ever after in a low-key 1930s home owned by a string of Hollywood names before them.
Catherine Zeta-Jones and Michael Douglas
When Catherine Zeta-Jones starred in “Zorro,” Michael Douglas was set on meeting her. Twenty years later, they are married with two kids. After 13 years of marriage, they hit a speed bump that took an eight-month separation to resolve.
Douglas said that he believes relationships can be repaired, but only if both parties are willing. “It can’t be a one-way street,” he shared with Ellen DeGeneres on her show in 2014.
More Than 30 Years of Snoop Dogg and Shante Broadus
Snoop and his wife Shante Broadus married in 1997. Before Cordozar Calvin Broadus, Jr. became the world-famous Snoop Dogg, he and Shante Taylor attended high school together and even went to prom. But in 2004, Snoop was so serious about straying, he filed for divorce.
After realizing how good he had it, he and Shante renewed their vows in front of 200 guests. The couple was brought together, in part, over their daughter’s lupus diagnosis. He told MTV, “I was trying to get a divorce, but I went back home, and I fell back in love with my wife and kids.”
Patrick Dempsey and Jillian Fink
Just one look and no one is surprised that People magazine named Patrick Dempsey “Sexiest Men Alive” two years in a row. The “Grey’s Anatomy” heartthrob met his wife Jillian Fink, a celebrity stylist. He sat in her chair, and they married in 1999. They have three children and a loving family. But in 2015, Jillian filed for divorce after a scandal blew up.
Dempsey reconciled with his wife, choosing his family-man lifestyle over an extramarital affair with a “Grey’s Anatomy” staffer.
Judges Judy and Jerry Sheindlin
Judge Judy and former New York Supreme Court Justice, Judge Jerry Sheindlin, have been married for over four decades. They met at a bar in 1976. Judy Sheindlin was a prosecuting attorney and Jerry was a defense attorney. With her father’s death in 1990, things changed.
The emotional toll on Judge Judy led to dissolution. She threatened Jerry with a divorce. He said, “Oh, yeah? I dare you.” The next day, in full Judge Judy fashion, the papers were filed. They parted for a year but couldn’t stay apart.
Nick and Vanessa Lachey
Nick and Vanessa first laid eyes on each other at an MTV studio in 2006. That same year, Vanessa starred in Nick’s music video, a song about his breakup with Jessica Simpson, which also went down that same year. Nick and Vanessa kept their love to themselves until announcing it to the world with a kiss on MTV’s New Year’s Eve special.
2007 fired up their relationship, but 2009 doused the flame with a brief breakup. The lovebirds married in 2011 after the former 98 Degrees boy band popstar proposed to her on both knees.
High School Sweethearts Thomas Rhett and Lauren Atkins
This couple has one of the most adorable love timelines in the entertainment industry. Country singer Thomas Rhett wrote the hit song “Die a Happy Man” about marrying Lauren Atkins, and also “Marry Me,” from the same album. These lovebirds met in first grade. They dated in high school at age 15. Going off to college, both nearly married someone else.
But Lauren’s father intervened by calling up Rhett and bringing them together. Now, they are blissfully married with three daughters.
G.O.T. Rose Leslie and Kit Harington
“Game of Thrones” star Kit Harington said in 2014 that there wasn’t a parallel offscreen love affair between him and Rose Leslie. As it turned out, the couple did tumble into love just like Jon Snow and Ygritte. Everyone loves a good love story, and theirs is “highly romantic.” That is, at least, how Rose described Kit’s proposal.
She said it was “under a beautiful blanket of stars” in the English countryside. If that’s not romantic enough, they married in a castle in Scotland. But it almost didn’t happen. A 2017 April Fool’s Day joke nearly drove her away.
Karina Banda and Carlos Ponce
Puerto Rican actor Carlos Ponce and Univision reporter Karina Banda dated for 10 months. Just as the social media world began to fawn over the couple, Carlos went and shut down his Instagram account after announcing the breakup. The romance had taken them to Italy, Columbia, and England, but suddenly the amorous posts halted. It wasn’t the end.
The couple couldn’t stay apart. She said it was the happiest day ever when Carlos dropped the ring in Karina’s champagne, along with a toast. And then a secret wedding sealed the happy ending.
Dax Shepard and Kristen Bell
It’s quite to the contrary. This husband-and-wife duo agree that openness is the cure. “We don’t want anyone to think we met, and it’s been easy,” Dax said. “It’s a bad expectation to have.” Working things out, they saw the same therapist, separately, so they could complain about each other.
The Hollywood A-listers met in Italy in 2009 filming “When in Rome.” The proposal came via tweet by Bell in support of California’s 2013 Prop 8 reversal. They married the same year. Now the Shepards share two daughters. Dax loves playing drums in the family band with the girls on guitar.
Brian Austin Green and Megan Fox
It was back in 2004 when this pair first met on the set of “Hope & Faith.” With Brian 13 years Megan’s senior, it was awkward, but they ended up dating for a couple of years. The lovers got engaged in 2006. It fell off the table, unexpectedly, due to rumors regarding Megan and co-star Shia LaBeouf. A year later, Green and Fox got back together and quietly eloped on the Big Island.
Alas, the rocky relationship crashed on the crags once again after the birth of their second son. In 2020, on his May 18 podcast, Brian called it over. We’ll keep watching these two.
Justin Timberlake fawns over Jessica Biel
Justin Timberlake adores gushing over his beautiful wife. They’ve been together since 2007, and by 2015, with the birth of his first son, the former boy band actor says he loves Jessica Biel more than any song he could write. But he’s fallen off the wagon a couple of times. First, in 2010 with Olivia Munn and again in 2019 when Timberlake was spotted affectionately engaged with co-star Alisha Wainwright.
Apologies soon followed. He said it’s not the example he wants for his son. Now they have two boys. With almost a decade of marriage, Timberlake is still gushing over Biel.
Gold medalist Michael Phelps and Miss California Nicole Johnson
Michael Phelps and Nicole Johnson’s relationship has been full of ups and downs. Dating for eight years before the big day, the all-time record-breaking gold medalist went down on one knee to propose. Prior to Nicole, he had a record number of girlfriends.
Those eight years of dating put them through a lot, as Phelps said. But he loves “her to death.” What they’ve been through has helped them grow as a couple. He says they’re at a completely different level.
Marie Osmond and Steve Craig
Steve Craig and Marie Osmond met in the early 1980s. The famous diva married the Brigham Young basketball star in 1982. After three years, they went separate ways, but Osmond said she never loved or respected anymore more. Decades later, the couple reunited. They remarried in 2011 after dating secretly for two years.
She was 51 when they remarried. They sealed their vows with an 8-carat Asher diamond. She also donned the original ring Craig bought at an estate sale in France.
David Furnish and Elton John's
“We’ve had our ups and downs like every other couple,” Elton John said of the decades-long relationship. “Our love has grown stronger and stronger.” Rumors of Furnish being a control freak over the star’s fortune have surfaced. The loving couple married in 2014, as soon as same-sex marriage passed the parliament.
A Saturday note-writing ritual is part of the reason for their strong bond. The notes started as love letters but now they also work out problems that way. They share two young sons. The music man said having children is “the greatest thing you’ll ever know.”
Elizabeth Taylor and Richard Burton
In filming the ancient Egypt movie in Italy’s capital, Elizabeth Taylor and Richard Burton’s passion rivaled the legendary lovers. When the director called, “Cut!” the pair did not stop kissing. About a year after “Cleopatra” was released, the two married and it was hailed as the “marriage of the century.”
Burton was the leading lady’s fifth husband. After ten years they called it quits. Burton spammed her with love letters and begged her to return. She did. They married and divorced again. It lasted mere months. They stayed friends for the rest of their lives.
Gregg and NeNe Leakes
These two married in 1997, the first time. It’s been a roller coaster ride. “The Real Housewives of Atlanta” diva found her relationship with Gregg Leakes leading the reality TV drama. Her husband complained fame went to her head. In 2010, NeNe divorced him to teach Gregg a lesson, as she put it.
A year later, the pair hooked up again. By 2013, NeNe’s and Gregg’s second marriage was made into a Bravo special, “I Dream of NeNe: The Wedding.” Sadly, Gregg passed away on September 1, 2021.
Rhea Perlman and Danny DeVito
This comedian pair married way back in 1982, and they still love each other. It’s no secret the couple swerved and missed two divorces. 2012 was the first year they separated. That parting lasted a year. Then, in 2019, it looked like the two were heading to divorce court again, but time apart found the actors, who are both in their 70s, wanting to keep what they have.
Rhea said it’s true that, for a minute there, they were in each other’s face but now everyone is happy. They have three children and a wonderful family. Perlman says they agree on the important stuff.
Robert Wagner and Natalie Wood’s story
Natalie Wood’s breakout movie “Rebel Without a Cause” brought her an Oscar nomination. She earned two more nods from the Academy, and she was only 25. She fell in love with leading man Robert Wagner at 18 and they soon married. Her colossal fame sunk the ship before five years of marriage were up. She left him and married another man. But they couldn’t stay apart and remarried after she left her second husband.
Then, on a boating trip to Catalina, Wood was involved in a devastating accident. It was 1981 and Wagner, as late as 2018, is a person of interest. The investigation is ongoing.
Crystal Smith and Ne-Yo’s Breakup
Ne-Yo and Crystal took a four-month pause in their relationship to work through demons and sort out their differences. At the end of the day, they found that what they share is love. Crystal realized that she needed counseling because her anger was taking over. The reconciliation has been praised.
An “OWN” docuseries, “Behind Every Man” gives a behind-the-scenes look at their married life. The happy ending began with renewing their vows and continues at each other’s Instagram page. “I love you like lungs love oxygen,” wrote Crystal’s songwriter hubby on their six-year anniversary.
Odette and Dave Annable Are on Again
Nine years into their marriage, Odette and Dave called it quits. But nine months after they separated the actors who met on “Brothers & Sisters” were back together.
The announcement came via Instagram. Both posted a smoochy beach pic with matching messages: “2020. It ain’t all bad news. #TheAnnables.” Dave left this playful note on Odette’s post, “My post is better.”
Tristan Thompson and Khloé Kardashian
You can’t say they didn’t try. Khloé and NBA star Tristan Thompson met in 2016 and split twice. Their makeups were sugar-sweet on social media. And we saw every appearance of domestic tranquility with the couple on “Keeping Up With the Kardashians,” but they split again in 2021.
Tristan was unfaithful to Khloé which caused her to leave him twice. You can’t always get what you want, so Khloé got what she needed. Tristan and Khloé have a healthy co-parenting relationship for their daughter True.
Richard Pryor and Jennifer Lee
Richard Pryor lived a wild and crazy life. He was married seven times. Two of those marriages, however, were with Jennifer Lee. The legendary comic met Lee as an interior designer in his home. They were married a week after he proposed in the rainforests of Hana.
His wild and crazy side drove Jennifer to separate her from the man she loved just a year later. Jennifer remarried Richard in 2001, 19 years after the split. It followed his diagnosis with MS which took his life in 2005.
Kelly Ripa and Mark Consuelos from “All My Children”
The romance blossomed two decades ago. On a 1996 date, the two discovered they were soulmates. Mark proposed and the impatient couple flew off to Las Vegas and eloped. Kelly happened to have a gorgeous Barney gown in her closet.
This couple joyfully share one of the most passionate relationships in the celeb world. But they did have one breakup. Consuelos did not reveal the split until 2019. It happened a week before they set upon marrying.
Ben Stein and Alexandra Denman
“Bueller.” Ben Stein is most recognized as Ferris Bueller’s high school economics teacher. But the actor/comedian was also once a political speechwriter for Nixon. That was when he fell in love with Alexandra Denman. It was 1968 when they tied the knot.
A few years later, they decided that marrying was a mistake. The divorce was final in 1974. That was not the end of the story. In 1977, they married again, and they are still together.
Frida Kahlo and Diego Rivera
Frida was 15 when she set eyes on Diego. Two of the world’s most recognized 20th-century artists came together. He was a Cubist who reinvented Mayan mural art and she’s known for her magical realism folk art portraits. They met as members of the Mexican Communist Party in 1927 and married in 1929. It was eccentric to start. Diego had two common-law wives.
They were both unfaithful to one another but reconciled. By 1939, Diego filed for divorce. In 1940, they remarried but retained ongoing extramarital relationships. It’s not your conventional love story.
Sinbad and Meredith Adkins
Television personality Sinbad, a.k.a. David Adkins, said he married Meredith too early. It was 1986, and it lasted until 1992. But there is more to their story. In 2002, they vowed anew and have been happily married ever since.
They cohabitate these days, but Sinbad has credited living apart as the secret to their marital bliss. The couple is known for gushing over each other on social media.
Barbara Walters and Merv Adelson's second chance
The once-media power couple, Merv Adelson and the late Barbara Walters met at the peak of both of their careers. Barbara Walters, so prominent as a journalist, SNL ran a long-running skit in which Gilda Radner parodied the famous “20/20” celebrity journalist. Merv owned one of television’s most well-known production companies.
They married in 1981 when Merv was CEO of Lorimar Television. Just a few years later, the power couple split. They tried again in 1986. But sometimes giving it a second shot doesn’t work. Their marriage was strained by bi-coastal careers. It fell apart and divorce followed in 1992.
Jacqie Rivera and Michael Campos
Jacqie and Michael Campos married in 2012 and have four children. They dated for several years before linking for life. Jacqie is the daughter of the late actress, singer and producer, Jenni Rivera, and got into reality TV with her mother’s star power. There was a fall from their vows a few years into marriage.
In December of 2017, Jacqie announced to her Instagram followers that a divorce was imminent. Joy to the world, the couple reunited. A picture of the family together under the Christmas tree put any rumors to rest.
William Levy and Elizabeth Gutiérrez
William Levy and Elizabeth Gutiérrez met on the set of a Telemundo telenovela in 2003. The beautiful couple who has two children have never officially married, but they have had their share of ups and downs. Break up rumors naturally circle around the soap opera stars. Many questions about infidelity have circulated but the couple has never confirmed any.
In 2011, the rumors got real, and Gutiérrez announced the split with the Cuban heartthrob. They gave it another chance and they have one of the most enduring relationships in Latino entertainment.
Ed Sheeran and Cherry Seaborn
Ed Sheeran and Cherry Seaborn engaged in 2017 and married in 2018. 2020 brought a baby girl into their lives. But their connection goes back much further. It was in high school in Suffolk, musician Sheeran developed a huge crush on Cherry.
They met up again in 2015 and can’t get enough of each other. She is Sheeran’s muse. His songs “Photograph” and “Shape of You” were inspired by having Cherry in his life.
Ashley Iaconetti and Jared Haibon
Jared proposed to Ashley in 2018. The pair married in 2019, but it was a bumpy ride getting there. It was love at first sight when they met on the second season of “Bachelor in Paradise,” at least for Ashley. Jared wasn’t on board. In 2018, surprise, surprise, Jared wooed Ashley with a love letter.
The following season was not smooth sailing. Rough waters threatened to capsize their love boat in 2016 with Jared’s eyes straying to Caila Quinn. But these days it’s a tale of happily-ever-after crowned by news of a baby boy.
Adorable Rachel Bilson and Hayden Christensen
The Hollywood couple hooked up for the first time co-starring in “Jumper” (2008). Daughter Briar Rose arrived in 2014 but they called it off and the two split in 2018. A long-distance relationship was perhaps to blame. Breakups post-baby are all too common. Couples struggle to navigate parenting.
At the time of the split, they were together 10 years. So, maybe in the future Rachel and Hayden will go back “on” in this on-and-off relationship.